


Nice Guys Finish Last

by Haunt_Haunt_Haunt



Category: Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Alcohol, Aromantic, Bisexual Bede, Bisexual Leon, Casual Ableism, Casual Sex, Comedy of Errors, Crack Treated Seriously, Fade to Black, I Can't Believe I Wrote This, I'm Sorry, If Rose Knew He'd Die, Multi, Nudes, Oleana is FILTHY, Public Nudity, Sexting, Slut-Encouragement, aro not ace, it's exactly as bad as it sounds, reddit, thots
Language: English
Status: Completed
Published: 2020-12-17
Updated: 2020-12-17
Packaged: 2021-03-11 00:34:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,269
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28126197
Author URL: https://archiveofourown.org/users/Haunt_Haunt_Haunt/pseuds/Haunt_Haunt_Haunt
Summary: Oleana takes a day off. Only someone that classy can have a day that trashy.
Relationships: Beet | Bede & Olive | Oleana, Olive | Oleana & Rose | Chairman Rose, Olive | Oleana/Dande | Leon
Comments: 5
Kudos: 7





	Nice Guys Finish Last

**Author's Note:**

> Do not sue, I am poor.

The alarm went off at 5 sharp. She pressed the snooze button precisely three times, then when it went off the final time, she got up, turned it off, then went directly to the shower. Her shower lasted approximately ten minutes. She would wash her hair, then her body, then condition, then get out. After that she moved immediately to the mirror, brushed her teeth, hit her hair with the diffuser, put on her clothes that were laid out the night before, then did her makeup. Her morning routine took a grand total of thirty minutes with a three minute differential to account for things like the weather. After that, she went directly to the kitchen, pulled out a bagel, put on a considerable amount of cream cheese, then left, heading immediately to the train station to start work. This was her normal day. It was quick, it was efficient, and it was practiced. It was her normal routine for the past seven years, and she didn’t deviate from it.

Except she did. She deviated from this strict schedule one day a month. It was the only way she could put up with the rest of the month, and she so looked forward to it.

The buzzing alarm didn’t wake her up. She had unplugged it the night before, and had turned off the phone too. She had filled out this day for PTO a month ago. She earned this. Instead, she rolled out of bed when she woke up naturally and checked her watch, which was incapable of waking her up. It was eight in the morning and she smiled, fluffing out her hair. She’d slept in, and it felt wonderful. Now to check on what she had planned.

Mostly she wanted to go with the flow of the day, but a pence of planning is worth a pound of cure and whatnot, so she at least had some idea. First, she had to check on the boy. See, Oleana didn’t have time for a relationship. She was already in one, and he was an absolute man-baby. She liked Rose okay, but Rose was an abysmal business man, and often the day-to-day running of Macro Cosmos fell to her. She had no idea how he had even become the chairman. He couldn’t delegate or manage his way out of a paper sack. So, on her day off she liked to find a guy and fuck his brains out. The goal was to find the exact opposite of Rose, and that was proving harder and harder every year as she got older, but she hadn’t had any issues this month. Apparently this one liked a cougar.

She sat at her computer, not bothering with trivialities like a bra or underwear. She was near the top of a Wyndon skyscraper, and if there was a passing helicopter or an enterprising young man with a telescope then she hoped they appreciated the view. She turned it on, waited for it to boot up, then opened her throwaway account on Reddit. Of course, no one knew it was her. She went to great pains to make sure her once-a-month Reddit life was a secret. Once she had it booted up, she went straight to her messages. She met this one on the r/hookup subreddit, where she normally went. She demanded pictures up front, no funny business, and they had to be under thirty but over twenty-one, and she actually got a reply. He didn’t want to say where he was from and normally that would count as funny business, but he was absolutely up-front and honest about everything else and was positively charming. They’d been swapping nudes for a few days even though she had a strict policy about that. He was just that persuasive.

Pickings were slim the month before and she found someone, but he wasn’t her type at all. He was this big jock type with a mommy fetish. That wasn’t her thing and that was the only time she had ever asked someone to put their pants back on and leave in the middle of getting railed from behind. This one was way more her type. She opened the messages and there was his dick, just right there. He had a nice one too. She could tell from the angle that he was a smooth guy. He had muscle, but not like a jock, and he kept himself groomed. There was a small and well-maintained patch of blonde pubic hair. His dick was nice and thick, and she was going to enjoy choking on it later. The thought was already turning her on. God, she loved her days off.

MsNickit: Hey, we still on for tonight?

She hadn’t expected him to respond so soon, but was pleasantly surprised when the little icon appeared showing he was writing.

PinkTwink: Yes ma’am. I left home on a Corviknight a few minutes ago. I should be in Hammerlocke by lunch, and from there, I can catch a train to Wyndon.

MsNickit: Good boy. Eat before you arrive, preferably fruit, and drink lots of fluids. I expect you here at 7, sharp.

PinkTwink: Yes ma’am!

She bit her lip. It was always good when they listened. When they obeyed. Good boys get to cum inside, after all. If anyone knew how much of a slut she actually was, she’d be disgraced. She scrolled back up to the picture and slipped her fingers between her legs, rubbing just slightly and closing her eyes. She imagined how good and stuffed he was gonna make her, and how she’d make him beg to cum inside. Then how she’d clean off his cock with her mouth and get him off again. They normally broke after round three, but she liked to see how far they could go, and this one behaved.

She stopped rubbing herself, aroused but not willing to cum. She’d edge like this throughout the day so that her orgasm was that much harder later. Instead she stood and went into her bedroom and pulled on leggings and a tee shirt, then grabbed a pair of sunglasses and a big hat. The last thing she wanted was to be recognized on her day off. That had happened once. It was horrible.

After she was dressed, she let her pokemon out to roam the apartment and made sure the food was full, then grabbed her overnight bag and keys. She wouldn’t be back to the apartment tonight. She’d return in the morning to get her phone and put her pokemon back up. She closed the door and headed down the elevator, then hit the Wyndon streets. Step one was breakfast, and she made her way to her favorite place on earth. On a normal day, it was a bagel, but not her day off.

She walked into the Krispy Alkreamie and ordered not one, but two donuts. If she went out with Rose, as he insisted every now and then, she’d get regular glazed. She liked it fine; it was sweet but not too sweet and it didn’t get everywhere. Not today though. A few minutes later, the guy at the counter brought her these sloppy dark chocolate donuts covered in salted caramel drizzle. She didn’t even bother to keep it off her perfectly manicured nails and bit into one, the caramel covering her fingers. With her clean hand she checked her second phone, the one that didn’t have work stuff on it, and played Oran Berry Burst while she ate. It was a game where you tried to match berries with their counterparts to get the highest score. She was on level 237. 

Any other day, she would have eaten and been good to go in twenty minutes, but not today. Today she took her time, depositing her tray and thanking the cute boy behind the counter after an hour then went back out onto the street again. Next was to head to the stylist. She checked her phone on the way.

PinkTwink: Thinking about you has me so hard, I’m throbbing.

She smiled. He was such a sweet boy. She decided on something risky and ducked into an alley, then when she was certain no one saw her, she pulled up her shirt, then down her bra and snapped a picture of her bust, then sent it.

MsNickit: I’m positively dripping thinking about your cock, beau. I can’t wait to get my lips around it.

PinkTwink: Which lips?

MsNickit: That depends on how good you are, doesn’t it?

She didn’t wait for a response and stepped back onto the street and headed to the stylist. Her stylist was the only one that got to see her without the disguise on her day off.

“Hey Ms. Oleana,” she said as Oleana walked in. “Are we doing the usual today?”

“I think so, but you’re the artist, as ever. I have a hot date tonight, so I need to look exceptional.”

“Absolutely. Is he cute?”

“He’s something, but I have no pictures I can show you.”

“Ms. Oleana!” The stylist said with a laugh, and they talked while she did Oleana’s hair. They got rid of the dead ends, then did a hot oil treatment, then did some styling, making it curl at the end. After that, Oleana checked her watch. She had just enough time for a late lunch, then she’d go book the hotel room and get ready for her boytoy.

Her room was at the Rose of the Rondelands, and it wasn’t for any reason other than she liked to make this place as filthy as possible. That, and the view was nice. She booked her room, went up to it, then turned on the radio and started to get ready. First was the shower. She had to pile up her hair to not get it wet and put on a shower cap. After that, she got into her night bag. She came across as a domme, but you have to be that way when you work with educated idiots like Rose. She actually was fairly willing to do just about anything the partner could think of, and it led to some pretty interesting experiences.

First, she put on the corset that was more aesthetic than a real corset. She laid it on the bed then laced it up and snapped it closed. Next came the black lace thong, then the garters. After that she pulled on the hose and attached them to the garters, then put on her knee-high boots that cost as much as a car. Afterwards she let her hair down from the cap, put on her dark ruby lipstick (and not the good stuff. If it didn’t smear, it wasn’t as fun) and black eyeliner with wings, and then there was a knock on the door. Right on time.

She made her way over to the door, leaned on the doorframe in her best sexy pose, then opened the door with a smile that very quickly turned into a gape. Her eyes got wide, and she was about as surprised as the young man that was at the door.

“Uhh…” Bede said, looking at her crotch then very quickly back to her face again. “Ms… Ms. Oleana?”

Oh no. Nononononono. How? How had she… She was so careful! Oh god she’d seen his dick! Oh god, she liked it! It took her a minute to speak through the shock. “Get…Get in here.”

“No!” Bede shrieked.

“GET IN HERE NOW, YOUNG MAN.”

He wanted to run, but something in her tone said that if he ran she’d run him down like an angry Tauros and eat him whole while he screamed. He came into the room and she firmly shut the door and locked it, then crossed the room and opened the minifridge, withdrawing two of the bottled daiquiris that she had bought for the night.

She turned back to Bede. He was shaking. At least he was having as good a night as she was. 

“Sit down.”

He did so immediately, and she sat across from him and slid the daiquiri over to him. “Here’s what we’re going to do. We’re going to drink these daiquiris, we’re going to watch TV, and we’re going to bitch about people we don’t like. And we are never going to speak of this. Never. Ever. Again. Am I clear, Bede?”

“Y… yes ma’am.”

“Don’t call me that.”

“Sorry, Ms. Oleana.”

The next morning, her alarm went off at five sharp. She pressed the snooze button precisely three times, and then she got up, turned it off, then went into the shower. She washed her hair first, then her body, then conditioned. Then she stepped out, dried off, and brushed her teeth, put on her clothes that she laid out the night before, then did her makeup. After that, she went into her kitchen and put a bagel in the toaster, then put on a considerable amount of cream cheese. It was this again. This for a whole other month. At least the night wasn’t a total bust. She was still horny after Bede went home early in the morning, but she found someone awake.

She turned as he walked into the kitchen, not even bothering with clothes.

“How’d you sleep, Leon?”

“Mmm.” He said with a small laugh. “Like a rock.”

She leaned over to him. “Be a good boy then, and when I get back, we can do it again.”

“Yes ma’am.”

She glanced at the door then down at his cock. Eh, what was another five minutes?

**Author's Note:**

> If you liked it, smash that Kudos and let me know!


End file.
